US6183942B1 - Thinner composition for removing spin-on-glass and photoresist - Google Patents

Thinner composition for removing spin-on-glass and photoresist Download PDF

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US6183942B1
US6183942B1 US09/429,535 US42953599A US6183942B1 US 6183942 B1 US6183942 B1 US 6183942B1 US 42953599 A US42953599 A US 42953599A US 6183942 B1 US6183942 B1 US 6183942B1
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photoresist
edge
thinner composition
thinner
substrate
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Byung-Uk Kim
Ji-Hum Baik
Chang-Il Oh
Sang-Dai Lee
Won-Lae Kim
Chong-Soon Yoo
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Dongjin Semichem Co Ltd
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Dongjin Semichem Co Ltd
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    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/26—Processing photosensitive materials; Apparatus therefor
    • G03F7/42—Stripping or agents therefor
    • G03F7/422—Stripping or agents therefor using liquids only
    • G—PHYSICS
    • G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
    • G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/16—Coating processes; Apparatus therefor
    • G03F7/168—Finishing the coated layer, e.g. drying, baking, soaking

Definitions

  • the present invention relates to a thinner composition for removing spin-on-glass and photoresist which is used in the semiconductor component manufacturing process. More particularly, the present invention relates to a thinner composition that can be used in washing and removing the unnecessary spin-on-glass (“SOG”) of an SOG layer at edges and a backside of a substrate, the SOG layer being produced when an oligomer solution of an organic silicon compound having a siloxane bond is spin-coated on a substrate during the formation of an intermediate insulated layer. The present also relates to a thinner composition that can be used in washing and removing photoresist from the edges and the backside of a substrate, the photoresist being used as a mask in a photolithography process.
  • SOG unnecessary spin-on-glass
  • LSI Large Scale Integrated circuits
  • the component height of metal wiring, etc. has withnessed only minimal reductions so as not to increase wiring resistance and electric current density. Therefore, as side gap dimensions between metal wirings are becoming extremely narrowed, wiring height must naturally increase.
  • this type of wiring is formed by high anisotropic etching, the edges of the wiring have a sharp slope, and the number of wiring crossings and holes increase. Furthermore, the surface topography of LSI chips becomes greater due to the multi-layering of the wiring.
  • anisotropic wiring etching can leave residue at the sides of walls where there is a substrate topography that can lead to short circuits.
  • SOG spin-on-glass
  • n is an inter equal to or greater than one.
  • Patents including Japanese Laid-open Patent No. Heisei 9-36110, and Japanese Laid-open Patent No. Heisei 8-203876.
  • the insulated layer of silicon oxide material is made by heated condensation polymerization.
  • a solution is used to penetrate into the microscopic wiring, filling in level differences to be evened out.
  • a low temperature process is possible as condensation polymerization occurs below 400° C.
  • regular processing technologies such as the conventional etching, etc., can still be employed as the resulting insulated layer is a silicon oxide substrate.
  • a thinner composition can remove the SOG coating at the edges and backside of the substrate quickly and thoroughly. It is also useful in removing undesired photoresist generated when a photosensitive resin composition is spin-coated.
  • the photoresist is used as a mask in the photolithography process for the microscopic circuit patterning.
  • the photolithography process in the semiconductor component manufacturing process is an electronic circuit forming technique accomplished through the steps of coating a photoresist on a substrate, transferring a pattern according to the original design, and cutting according to the transferred pattern, i.e., the etching process.
  • This photolithography process is performed through various processes including:
  • these edge beads of photosensitive materials can be produced after the spin-coating process in which a photoresist is applied to a substrate and the substrate is then rotated making the photoresist spread out evenly on the surface by the action of centrifugal force.
  • Photoresist inclined toward the edge and backside regions of a substrate by the centrifugal force is formed into small spherical shapes in this spin-coating process.
  • This spherical shapes can be a source of particles in the apparatus after it is passed through the baking process and can be released during the transportation of a substrate, or can become a source of defocus during the light exposure process.
  • a spray nozzle is installed at edge parts of the substrate and at the upper and lower backside parts. A thinner composition composed of organic solvent constituents is sprayed through the nozzles to remove these excess photosensitive materials.
  • a positive type chemically amplified resist was suggested in literature as an alternative for this (Proc. SPIE., Vol. 1262, p32, 1990).
  • This chemically amplified resist has a multi-constituent composition comprising an acid generator which produces acids when it is irradiated, and a compound which is reacted by these acids.
  • a polymer compound which is reacted by these acids is known to have a structure as represented in General Formula 2:
  • n is an inter greater than or equal to one
  • R is an alkoxycarbonyl group, alkyl group, alkoxyalkyl group, alkylsilyl group, tetrahydropyranyl group, alkoxycarbonyl methyl group, etc., compounds which can be easily decomposed when reacted by acids.
  • a polymer compound such as a polyvinyl phenol derivative in which photoabsorption occurs in the short wavelength range, the chemically amplified resist becomes more transparent, and has a high sensitivity and resolution as a resist reaction progresses by a chain reaction due to an acid catalyst.
  • a polyvinyl phenol derivative receives a strong multiple reflection effect by light reflected from a lower part of the substrate due to a high transmittance of excimer laser light as described in the above. Multiple reflections within a membrane are generated by interference between the irradiated light (1) and the reflective light from a lower part of the substrate as shown in FIG. 5 .
  • FIG. 6 shows that the pattern dimensions vary greatly according to a thickness of the resist film.
  • the reflective light interference caused by topography on a semiconductor substrate affects the pattern dimension greatly in case of exposure with a mercury light.
  • light entering can cause a diffused reflection at an area with different levels generating a halation phenomena, resulting in pattern flow. Consequently, an excellent resist pattern is not formed.
  • the light interference conditions in a resist layer vary causing pattern dimension changes.
  • the ratio of a minute pattern height and width can not be controlled as the proximity effect is generated by the rear dispersion of electrons.
  • a multilayer resist system using a spin-on-glass coating was suggested (Japanese Laid-open Patent No. Heisei 3-203240) as a method for resolving these problems caused by protrusions and depressions of a substrate surface.
  • a multilayer resist system is a method in which a thick first organic resist layer having high absorbance is coated over the entire surface of the substrate so that protrusions, depressions and topography are planarized.
  • a thin second resist pattern is formed on the first organic resist layer using commonly known photolithography techniques, and this resist pattern is transferred to the above thick first organic resist layer so that an exposed area of the above substrate can be etched.
  • the thick first organic resist layer can be directly etched using the above second resist pattern as a mask, it is also good to etch an exposed part of the first organic resist layer using a SOG coating as a mask after a middle layer, such as highly etched resistant spin-on-glass, is formed between both layers, and unnecessary parts of this SOG middle layer are removed.
  • a middle layer such as highly etched resistant spin-on-glass
  • protrusions, depressions and topography on the substrate surface were planarized by the first organic resist layer having high absorbance, and a light, which passes from the top through the second resist film formed on the first organic resist layer, is absorbed by the first organic resist layer. Therefore, halation caused by reflection and dispersion of light from the substrate surface, or light interference in the resist film can be reduced, thereby preventing pattern shape dispersion or dimension change.
  • This method using a multilayer resist system has an advantage in that a high degree of applications are possible with the photolithography as the first resist layer controls the resist pattern characteristics as a mask, and the second resist layer, required for photosensitivity and resolution, can be bonded freely.
  • this method can be easily applied to extreme ultraviolet photolithography in which an extreme ultraviolet excimer laser light as an excimer light source is employed by using the first resist layer having excellent dry etching resistance and the second photosensitive resist having the high sensitivity and resolution with an extreme ultraviolet excimer laser light with a wavelength of less than 300 nm.
  • the thinner composition can be used in washing and removing undesired coating on the edges and backside of the substrate through such processes as the coating of an SOG solution in order to form an intermediate insulated layer in the semiconductor multi-layer wiring process, to improve layer flatness, in the process of coating the middle layer SOG solution for a multilayer resist system, or in the process of coating each photoresist that is used as a mask in the photolithography.
  • a dissolution rate and volatility may decide the performance of the above thinner composition.
  • a thinner composition dissolution rate as a capability of how effectively and quickly spin-on-glass and photoresist can be dissolved and removed, is crucial.
  • a smoothly treated profile like that shown in FIG. 2 can be made only by a proper dissolution rate in case of an edge area rinsing.
  • a photoresist attack can appear in the rinsing of a photoresist which is coated on a substrate as shown in FIG. 3 .
  • a flow phenomena of the partially dissolved photoresist tailings in the rinsing of a coated photoresist on the substrate can occur as shown in FIG. 4 .
  • a low rotation speed is now essential during the rinsing process with larger caliber rotational coaters.
  • volatility is required so that a thinner is easily evaporated in order that it does not remain on a substrate after the spin-on-glass coating and photoresist are removed.
  • the volatility is too low such that a thinner can not be evaporated, the remaining thinner itself serves as a contamination source in the each of the later processes, particularly in the subsequent etching process, etc.
  • the volatility is too high, the substrate is too rapidly cooled so that the variations in film thickness of the spin-coated spin-on-glass and photoresist are increased.
  • easy volatility even during handling can result in contaminating the clean room itself. This in itself causes a variety of faults, such as tailings or photoresist attack, and becomes a direct source for a decrease in semiconductor component manufacturing productivity.
  • the solvents for washing and removing photoresist include ether and ether acetate groups such as cellosolve, cellosolve acetate, propyleneglycol ether, propyleneglycol ether acetate, etc; ketone groups such as acetone, methylethyl ketone, methylisobutylketone, cyclohexanone, etc; and ester groups such as methyl lactate, ethyl lactate, methyl acetate, ethyl acetate, butyl acetate, etc.
  • ether and ether acetate groups such as cellosolve, cellosolve acetate, propyleneglycol ether, propyleneglycol ether acetate, etc
  • ketone groups such as acetone, methylethyl ketone, methylisobutylketone, cyclohexanone, etc
  • ester groups such as methyl lactate, ethyl lactate, methyl
  • PMEA Propyleneglycol monomethylether Acetate
  • ethylene glycol monoethyl ether acetate is excellent in terms of its dissolution rate, there are problems in that its volatility and flammability are high, and it is particularly toxic and associated with leukopenia and stillborn problems.
  • Propylene glycol monomethyl ether acetate contains ⁇ type of materials from its manufacturing processes, and has toxicity problems that may cause birth defects and otherwise be problematic to pregnant mothers.
  • Ethyl lactate can not obtain a sufficient rinsing effect by itself due to its high viscosity and low dissolution rate, and acetone, methylethylketone, etc., have problems of low workability due to their low flash point.
  • a mixed solvent composed of a pyruvic acid alkyl based solvent and methyl ethyl ketone was used as a thinner in Japanese Laid-open Patent No. Heisei 4-130715.
  • a thinner composition composed of a mixture of propylene glycol alkylether and a 3-alkoxypropionic acid alkyl group was used in Japanese Laid-open Patent No. Heisei 7-146562.
  • a thinner composed of a mixture of propylene glycol alkylether and butyl acetate, and ethyl lactate, or a mixture of butyl acetate, ethyl lactate, and propylene glycol alkylether acetate was used in Japanese Laid-open Patent No.
  • Heisei 7-128867 A thinner composed of a mixture of propylene glycol alkylether propionate, and methylethyl ketone, or a mixture composed of propylene glycol alkylether propionate, and acetic butyl ester/butyl acetate was used in Japanes Laid-open Patent No. Heisei 7-160008. Also, a mixed solvent composed of propylene glycol alkylether acetate, and propylene glycol alkylether was used as a thinner in U.S. Pat. No. 4,983,490, and a mixture composed of ethyl lactate and methyl ethyl ketone was used as a thinner in U.S. Pat. No. 4,886,728.
  • a mixed solvent composed of a pyruvic acid alkyl based solvent and methyl ethyl ketone cannot easily dissolve a 1,2-naphthoquinonediazide based photosensitizer (having a high esterification ratio among photosensitizer, and being a main constituent of photoresists).
  • a high volatility solvent such as a mixed solvent composed of propyleneglycol alkyl ether propionate and butyl acetate for rinsing the backside of the substrate cools the substrate and verifies a thickness of photoresist
  • a low volatility solvent such as a mixed solvent composed of ethyl lactate and methyl ethyl ketone reduces the rinsing capability on the substrate edge area.
  • solvents such as methyl pyruvate, ethyl pyruvate, etc., are known to corrode metal parts in the used photoresist reservoir fixed to a photoresist spin-coater after prolonged use.
  • propylene glycol monomethyl ether is known to have an advantage that increases the photosensitivity of photoresist compared to the conventional ethylene glycol monoethyl ether, i.e., a higher dissolution on photoactive compounds, it can cause discomfort to people due to its bad odor and somatological concerns.
  • propylene glycol monomethyl ether acetate as a method to mitigate these problems (U.S. Pat. No. 4,983,490), the problems nevertheless remain.
  • the most desirable effects are obtained in removing an undesired coating at the edges and a backside of a substrate which is produced in the spin-on-glass spin-coating processes that are used for integrated circuit component multilayerization such as applying an intermediate layer, planarizing sublayer, or a middle layer of a multi-layer resist system.
  • the present invention provides a mixed thinner composition in which propyleneglycol monoalkylether is mixed with monooxycarbonicacid ester, alkyl ethanoate, and alkyl lactate.
  • FIG. 1 is a plan view showing a substrate that has been spin covered with a coating liquid
  • FIG. 2 is an enlarged scanning electron microscope (SEM) photograph of a substrate edge area (inside the dotted line area of FIG. 1) taken after the coated substrate has been rinsed cleanly;
  • FIG. 3 is an enlarged scanning electron microscope (SEM) photograph of a substrate edge area (inside the dotted line area of FIG. 1) showing the photoresist attack phenomena which can result from a washing and removing procedure of the coated substrate;
  • FIG. 4 is an enlarged scanning electron microscope (SEM) photograph of a substrate edge area (inside the dotted line area of FIG. 1) showing the photoresist tailing phenomenon which can result from a washing and removing procedure of the coated substrate;
  • FIG. 5 is a sectional view showing a multiple reflective effect of a photoresist coated substrate where 1 represents irradiating light, 2 represents a substrate, 3 represents a level difference, and 4 represents photoresist.
  • FIG. 6 shows the dimensional change of a pattern by the variation of the photoresist film thickness
  • FIG. 7 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photoresist A with a thinner composition of EXAMPLE 1 indicated in Table 8;
  • FIG. 8 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photoresist A with a thinner composition of the EXAMPLE 2 indicated in Table 8;
  • FIG. 9 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photoresist A with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 8;
  • FIG. 10 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 8;
  • FIG. 11 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of EXAMPLE 1 indicated in Table 8;
  • FIG. 12 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of EXAMPLE 2 indicated in Table 8;
  • FIG. 13 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 8;
  • FIG. 14 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 8;
  • FIG. 15 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of EXAMPLE 1 indicated in Table 8;
  • FIG. 16 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of EXAMPLE 2 indicated in Table 8;
  • FIG. 18 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 8;
  • FIG. 19 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of EXAMPLE 1 indicated in Table 8;
  • FIG. 20 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of EXAMPLE 2 indicated in Table 8;
  • FIG. 21 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 8;
  • FIG. 22 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 8;
  • FIG. 23 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of EXAMPLE 1 indicated in Table 12;
  • FIG. 24 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of EXAMPLE 2 indicated in Table 12;
  • FIG. 25 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 12;
  • FIG. 26 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 12;
  • FIG. 27 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of EXAMPLE 1 indicated in Table 12;
  • FIG. 28 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of EXAMPLE 2 indicated in Table 12;
  • FIG. 29 is a scanning electron microscope (SEM) photograph of an 5 edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 12;
  • FIG. 30 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 12;
  • FIG. 31 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of EXAMPLE 1 indicated in Table 12;
  • FIG. 32 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of EXAMPLE 2 indicated in Table 12;
  • FIG. 33 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 12;
  • FIG. 34 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 12;
  • FIG. 35 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of EXAMPLE 1 indicated in Table 12;
  • FIG. 36 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of EXAMPLE 2 indicated in Table 12;
  • FIG. 37 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 12;
  • FIG. 38 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 12;
  • FIG. 39 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of EXAMPLE indicated in Table 13;
  • FIG. 40 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of EXAMPLE 2 indicated in Table 13;
  • FIG. 41 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 13;
  • FIG. 42 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin A with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 13;
  • FIG. 43 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of EXAMPLE 1 indicated in Table 13;
  • FIG. 44 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of EXAMPLE 2 indicated in Table 13;
  • FIG. 45 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 13;
  • FIG. 46 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin B with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 13;
  • FIG. 47 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of EXAMPLE 1 indicated in Table 13;
  • FIG. 48 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of EXAMPLE 2 indicated in Table 13;
  • FIG. 49 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 13;
  • FIG. 50 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin C with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 13;
  • FIG. 51 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of EXAMPLE 1 indicated in Table 13;
  • FIG. 52 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of EXAMPLE 2 indicated in Table 13;
  • FIG. 53 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 13;
  • FIG. 54 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a photosensitive resin D with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 13;
  • FIG. 55 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a spin-on-glass (SOG) solution with a thinner composition of EXAMPLE 1 indicated in Table 15;
  • FIG. 56 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a spin-on-glass (SOG) solution with a thinner composition of EXAMPLE 2 indicated in Table 15;
  • FIG. 57 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a spin-on-glass (SOG) solution with a thinner composition of EXAMPLE 3 indicated in Table 15;
  • FIG. 58 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a spin-on-glass (SOG) solution with a thinner composition of EXAMPLE 4 indicated in Table 15;
  • FIG. 59 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a spin-on-glass (SOG) solution with a thinner composition of COMPARATIVE EXAMPLE 1 indicated in Table 15;
  • FIG. 60 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a spin-on-glass (SOG) solution with a thinner composition of COMPARATIVE EXAMPLE 2 indicated in Table 15; and
  • FIG. 61 is a scanning electron microscope (SEM) photograph of an edge after the Edge Bead Removal test on a spin-on-glass (SOG) solution with a thinner composition of COMPARATIVE EXAMPLE 3 indicated in Table 15.
  • the present invention provides a thinner composition for washing and removing in semiconductor component manufacturing processes, in which the composition is a mixture comprised of propylene glycol monoalkyl ether, monooxycarbonic acid ester, alkyl ethanoate, and alkyl lactate.
  • propylene glycol monoalkyl ether of 40 to 80 wt % are mixed with monooxycarbonic acid ester of 10 to 30 wt %, and alkyl ethanoate of 1 to 20 wt % or alkyl lactate of 1 to 20 wt %.
  • the present invention can display excellent performance as a thinner composition for rinsing and resist removal when the above four constituents are properly combined with a specific constituent ratio.
  • composition of the present invention all of the above propylene glycol monoalkyl ether, monooxycarbonic acid ester, alkyl ethanoate, and alkyl lactate to be used are selected from an ultra pure semiconductor-grade of products, and the thinner composition is filtered with a 0.1 ⁇ m filter for very large scale integration (VLSI) device fabrication.
  • VLSI very large scale integration
  • Propylene glycol monoalkyl ether having an alkyl group with 1 to 5 carbon atoms in the above thinner composition can be used, including propyleneglycol monomethylether, propyleneglycol monoethylether, propyleneglycol monopropylether, propyleneglycol monobutylether, etc.
  • Propyleneglycol monomethylether from among these, has the most excellent dissolution on siloxane polymer, which is a SOG main constituent.
  • Monooxycarbonic acid ester is one constituent of the above composition, in which alkyl and alkoxy groups with 1 to 5 carbon atoms can be used. These compounds include 3-methoxypropionic acid methyl ester, 3-ethoxypropionic acid ethyl ester, 3-methoxypropionic acid ethyl ester, 3-ethoxypropionic acid methyl ester, 2-methoxyacetic acid methyl ester, 2-ethoxyacetic acid ethyl ester, 2-hydroxypropionicacid methyl ester, 2-hydroxypropionicacid ethyl ester, 2-hydroxypropionic acid propyl ester, 2-methoxypropionic acid ethyl ester, 2-ethoxypropionic acid propyl ester, 2-ethoxypropionic acid ethyl ester, ⁇ -methoxyisobutyric acid methyl ester, ⁇ -hydroxyisobutyric acid methyl ester, etc. 3-ethoxy propionic acid ethy
  • Alkyl ethanoate commonly called an alkyl acetate
  • Alkyl ethanoate is another constituent of the above composition in which an alkyl group with 1 to 4 carbon atoms can be used.
  • These compounds include methyl ethanoate, ethyl alkyl ethanoate, butyl ethanoate, etc.
  • Butyl ethanoate, from among these, is the most preferred in terms of the dissolution on a polyvinyl phenol resin, which is a binder resin of a excimer laser photoresist.
  • Alkyl lactate is another constituent of the present invention composition, in which an alkyl group with 1 to 4 carbon atoms can be used. These compounds include methyl lactate, ethyl lactate, butyl lactate, etc. Ethyl lactate, from among these, is the most excellent in terms of the dissolution on a photoactive compound of a photoresist.
  • propyleneglycol monomethylether is safer for humans during airborne exposure and is safer in the metabolism as it is rapidly decomposed into propyleneglycol and alcohol.
  • Physical properties include a boiling point of 132.8° C., a flash point (measured in the closed cup method) of 32° C., a viscosity (at 25° C.) of 1.86 centipoises (cps), a surface tension of 26.5 dyne/cm 2 , and a solubility parameter of 10.4.
  • the conventional thinner using ethylene glycol monoalkyl ether acetate only generates an unpleasant odor after use on spin-coater, and causes an unpleasant feeling (as it is known that if the thinner is used for a long time, fatigue is easily felt and the thinner negatively affects respiratory organs due to the fragrant property of volatile solvent).
  • a mixture solvent with monooxycarbonic acid ester can mitigate discomfort caused by an objectionable odor.
  • Monooxycarbonic acid ester can even be used, for example, as a fragrance.
  • monooxycarbonic acid ester has excellent dissolution properties on a polymer binder phenol resin among the photoresist represented in the below Table 1. These have 2 to 10 times better dissolution rates than the conventionally used ethyleneglycol monoalkylether acetate only.
  • Butyl ethanoate has an excellent dissolution rate on a variety of resins, and particularly low surface tension, as well as an excellent volatility such that excellent interfacial characteristics are achieved when a small amount of it is added to a thinner composition. Additionally, it can be seen in Table 1 that it has an excellent dissolution rate on polyvinyl phenol derivatives, a binder resin of short wavelength excimer laser photoresist composition and a siloxane oligomer solution, a main constituent of spin-on-glass.
  • Physical properties include a boiling point of 126.1° C., flash point of 23° C. (measured in a closed cup method), viscosity of 0.74 centipoises (at 25° C.), surface tension of 25 dyne/cm 2 , and a solubility parameter of 8.5.
  • Ethyl lactate has higher a solubility on photoactive compounds of photoresist than other solvents. However, it is difficult for ethyl lactate to be used as an independent thinner composition due to its high surface tension and viscosity, and a small amount, less than 1 wt % of the total thinner composition, can produce excellent characteristics when mixed with other thinners.
  • the present invention is applied by first properly combining the above four compositions with a certain constituent ratio, after which the above mentioned varieties of photoresist and spin-on-glass are coated by a spin-coater, and unnecessary edge beads are removed by dropping or spraying through a nozzle the thinner compositions on substrate edges and the backside thereof.
  • the supply quantity of a thinner composition can be adjusted according to the type of photoresist resins and spin-on-glass, film thickness, with the proper quantity generally selected from the range of 5 to 100 cc/min. After that, the substrate is dried through a spin dry process, and the micro pattern for semiconductor ICs can be completed through the subsequent photolithography process.
  • EGMEA represents ethylene glycol monoethyl ether acetate
  • PGME propylene glycol monomethyl ether
  • EPE represents 3-ethoxypropionic acid ethyl ester
  • MBM represents ⁇ -methoxyisobutyric acid methyl ester
  • PGMEP represents propylene glycol monomethyl ether propionate
  • BE represents butyl ethanoate
  • EP represents ethyl pyruvate
  • EL represents ethyl lactate
  • MEK represents methyl ethyl ketone.
  • Substrates used in the present examples were prepared as follows. Silicon oxide substrates having a diameter of 8 inches were used. These substrates were first rinsed in two baths respectively containing a hydrogen peroxide and sulfuric acid mixture (the substrates were dipped into each bath for 5 minutes), and washed with deionized water. This procedure was carried out in made-to-order washing equipment. After that, these substrates were spin dried in a spin drier (a product of VERTEQ Company, Model No. SRD 1800-6), and then photoresist was coated to a predetermined thickness on each of the substrate surfaces. A spin-coater (a product of Dainippon Screen Company, Model No. 80A) was used to coat photoresist.
  • a spin drier a product of VERTEQ Company, Model No. SRD 1800-6
  • the dissolving speed was measured using thinner compositions represented in Table 3 and conventional thinner compositions represented in Table 2 [G-line positive photoreist (a product of Dong Jin Chemical Ind. Co., Ltd., Product Name DSAM-300), I-line positive photoresist (a product of Dong Jin Chemical Ind. Co., Ltd., Product Name DPR-i5500), and Deep UV positive photoresist (a product of Dong Jin Chemical Ind. Co., Ltd., Product Name DHRK-200L)] that were selected from among photosensitive resin compositions commercially available.
  • a resist development analyzer (a product of Litho Tech Company, Model No. RDA-790) was used as a measuring unit, and the test results are represented in Table 4.
  • PGME propylene glycol monomethyl ether
  • EPE 3-ethoxypropionic acid ethyl ester
  • MBM represents ⁇ -methoxyisobutyric acid methyl ester
  • PGMEP propylene glycol monomethyl ether propionate
  • PGMEA propylene glycol monomethyl ether acetate
  • BE represents butyl ethanoate
  • EL represents ethyl lactate
  • BL butyl lactate.
  • the above thinner compositions can also be used for the purpose of recycling substrates by removing photoresists adhered to the surfaces of defected substrates from the photolithography process, or substrates that were randomly drawn out for process control testing.
  • the thinner compositions according to the present invention have excellent dissolution rates so that the process time can be shortened for substrate recycling.
  • edge photoresist was made under the conditions of Table 6 by supplying a thinner composition represented in Table 3 via an EBR nozzle onto a photoresist coated substrate represented in Table 5. All thinners were supplied from a gauge mounted pressurized vessel, the pressure was 1.0 kgf, and the flow rate of thinner from the EBR nozzle was 12 cc/min.
  • Photoresist A G line positive type DSAM-300 1.3 Photoresist B I - line positive type DPR-i5500 1.2 Photoresist C deep UV positive type DHRK-200L 0.9 Photoresist D deep UV negative type DHRK-N100 0.9
  • EBR Edge Bead Removal
  • An evaluation mark O indicates a clear edge shape after the EBR
  • an evaluation mark ⁇ indicates a distorted edge shape after the EBR caused by photoresist attack
  • X indicates the tailing phenomena of the edge film after the EBR.
  • FIG. 1 FIG. 8
  • FIG. 9 FIG. 10 after EBR test on photoreist A SEM observation FIG. 11 FIG. 12 FIG. 13 FIG. 14 after EBR test on photoresist B SEM observation FIG. 15 FIG. 16 FIG. 17 FIG. 18 after EBR test on photoresist C SEM observation FIG. 19 FIG. 20 FIG. 21 FIG. 22 after EBR test on photoresist D
  • the thinner compositions according to the present invention all show excellent performances (i.e., clear-cut edge shapes), while the conventional two constituent based thinner compositions show remarkable variation of results depending on photoresists, and reveal defected edge shapes on the whole.
  • the conventional two constituent based thinner compositions on a Deep UV positive photoresist can not prevent the severe occurrence of a tailing phenomena. This causes equipment contamination, etc., in the subsequent process, leading to reduced productivity in the semiconductor component manufacturing.
  • an evaluation mark O indicates a clear edge shape after the EBR
  • an evaluation mark ⁇ indicates a distorted edge shape after the EBR caused by photoresist attack
  • X indicates the tailing phenomena of an edge part after the EBR.
  • the thinner compositions according to the present invention maintain the equally excellent profile shapes even while varying the EBR rpm conditions. This means that a thinner composition according to the present invention shows not only an effect at the specific conditions, but also equal performance at various conditions, being more stable than the conventional thinner compositions under process condition changes.
  • test conditions were as follows.
  • a spin-on-glass (SOG) solution (a product of TOK Company, Model No. TCPS 190) of 1.5 ml was dropped on the center of an 8-inch silicon oxide substrate, a SOG composition was spun using a spin-coater at 50 rpm for 2 seconds. Then, the substrate was accelerated to 2800 rpm, adjusting the thickness of the SOG solution to a predetermined level. The SOG layer thickness was 0.3 ⁇ m at this time.
  • the EBR test conditions were as represented in Table 14, and an evaluation and the edge shapes resulting from the thinner compositions on SOG after the EBR test are provided in Table 15.
  • an evaluation mark O indicates a clear edge part shape after the EBR
  • an evaluation mark ⁇ indicates a distorted edge shape after the EBR caused by photoresist attack
  • X indicates the tailing phenomena of an edge part after the EBR.
  • the thinner compositions according to the present invention show excellent EBR effects on photoresists as well as on SOG. Therefore, in the semiconductor component manufacturing process, a single thinner composition can be used in the various process steps so that thinner supplying equipment compatibility can be obtained. Hence, the thinner supplying equipment and the process control are simplified, and costs are reduced.
  • the present invention provides the beneficial effect of substrate recycling and economical use in that a defective substrate can be reused by removing photoresists adhered to its surface. Additionally, substrates selected randomly for process control tests can also be easily recycled by utilizing this present invention.

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  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Materials For Photolithography (AREA)
  • Detergent Compositions (AREA)
  • Exposure And Positioning Against Photoresist Photosensitive Materials (AREA)
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US20060100116A1 (en) * 2004-11-05 2006-05-11 Echem Solution Corp. Photo resist stripper composition
US20080039359A1 (en) * 2006-02-13 2008-02-14 Gug-Rae Jo Cleanser for Slit Coater, Slit Coater for Manufacturing Display Device and Manufacturing Method for Display Device
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US6589719B1 (en) 2001-12-14 2003-07-08 Samsung Electronics Co., Ltd. Photoresist stripper compositions
US6682876B2 (en) 2001-12-14 2004-01-27 Samsung Electronics Co., Ltd. Thinner composition and method of stripping a photoresist using the same
US20040076910A1 (en) * 2002-04-06 2004-04-22 Shipley Company, L.L.C. Stripping method
US6878500B2 (en) * 2002-04-06 2005-04-12 Marlborough, Stripping method
US20080265159A1 (en) * 2002-04-17 2008-10-30 Ebara Corporation Sample surface inspection apparatus and method
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US8674317B2 (en) 2002-04-17 2014-03-18 Ebara Corporation Sample surface inspection apparatus and method
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US20050196974A1 (en) * 2004-03-02 2005-09-08 Weigel Scott J. Compositions for preparing low dielectric materials containing solvents
US20090298671A1 (en) * 2004-03-02 2009-12-03 Air Products And Chemicals, Inc. Compositions for Preparing Low Dielectric Materials Containing Solvents
US20050196535A1 (en) * 2004-03-02 2005-09-08 Weigel Scott J. Solvents and methods using same for removing silicon-containing residues from a substrate
US20060100116A1 (en) * 2004-11-05 2006-05-11 Echem Solution Corp. Photo resist stripper composition
US7456141B2 (en) * 2004-11-05 2008-11-25 Echem Solutions Corp. Photo resist stripper composition
US20080039359A1 (en) * 2006-02-13 2008-02-14 Gug-Rae Jo Cleanser for Slit Coater, Slit Coater for Manufacturing Display Device and Manufacturing Method for Display Device
US20120045617A1 (en) * 2010-08-19 2012-02-23 Sony Corporation Three-dimensional modeling apparatus, object, and method of manufacturing an object
US10022911B2 (en) * 2010-08-19 2018-07-17 Sony Corporation Three-dimensional modeling apparatus, object, and method of manufacturing an object
US11203149B2 (en) 2010-08-19 2021-12-21 Sony Corporation Three-dimensional modeling apparatus, object, and method of manufacturing an object
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US20160230129A1 (en) * 2015-02-06 2016-08-11 Dongwoo Fine-Chem Co., Ltd. Thinner composition
US9952510B2 (en) * 2015-02-06 2018-04-24 Dongwoo Fine-Chem Co., Ltd. Thinner composition
US10319227B2 (en) 2015-06-29 2019-06-11 Royal Truck & Equipment, Inc. Roadway work area safety truck
US11008717B2 (en) 2015-06-29 2021-05-18 Royal Truck & Equipment, Inc. Safety truck attachments, and methods of safety truck use
US11220659B2 (en) * 2018-08-31 2022-01-11 Enf Technology Co., Ltd. Thinner composition
JP2023098802A (ja) * 2021-12-21 2023-07-11 エーエーシー オプティックス （ナンネイ） カンパニーリミテッド グレーティング及びその製造方法、光導波路

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